Artaboterpenoids A and B, Bisabolene-Derived Sesquiterpenoids from Artabotrys hexapetalus.

Artaboterpenoids A and B (1 and 2), two novel bisabolene-derived sesquiterpenoids, were isolated from the roots of Artabotrys hexapetalus. Their structures with absolute configurations were elucidated by spectroscopic methods, and electronic circular dichroism (ECD) analyses. Notably, 1 featured a novel carbon skeleton with a new C-2-C-10 linkage, and 2a and 2b, a pair of enantiomers, represented the first examples of 1,2-seco-bisabolene-type sesquiterpene lactones. 2a exhibited cytotoxic effects against HCT-116, HepG2, A2780, NCI-H1650, and BGC-823 cell lines with IC50 values of 1.38-8.19 µM. Plausible biogenetic pathways for artaboterpenoids A and B were proposed.

Thiophenes, polyacetylenes and terpenes from the aerial parts of Eclipata prostrate.

One new bithiophenes, 5-(but-3-yne-1,2-diol)-50-hydroxy-methyl-2,20-bithiophene (2), two new polyacetylenic glucosides, 3-O-b-D-glucopyranosyloxy-1-hydroxy-4E,6E-tetradecene-8,10,12-triyne (8), (5E)-trideca-1,5-dien-7,9,11-triyne-3,4-diol-4-O-b-D-glucopyranoside (9), six new terpenoid glycosides, rel-(1S,2S,3S,4R,6R)-1,6-epoxy-menthane-2,3-diol-3-O-b-D-glucopyranoside (10), rel-(1S,2S,3S,4R,6R)-3-O-(6-O-caffeoyl-b-D-glucopyranosyl)-1,6-epoxy menthane-2,3-diol (11), (2E,6E)-2,6,10-trimethyl-2,6,11-dodecatriene-1,10-diol-1-O-b-D-glucopyranoside (12), 3b,16b,29-trihydroxy oleanane-12-ene-3-O-b-D-glucopyranoside (13), 3,28-di-O-b-D-glucopyranosyl-3b,16b-dihydroxy oleanane-12-ene-28-oleanlic acid (14), 3-O-b-D-glucopyranosyl-(1?2)-b-D-glucopyranosyl oleanlic-18-ene acid-28-O-b-D-glucopyranoside (15), along with fifteen known compounds (1, 3­7, and 16­24), were isolated from the aerial parts of Eclipta prostrata. Their structures were established by analysis of the spectroscopic data. The isolated compounds 1­9 were tested for activities against dipeptidyl peptidase IV (DPP-IV), compound 7 showed significant antihyperglycemic activities by inhibitory effects on DPP-IV in human plasma in vitro, with IC50 value of 0.51 lM. Compounds 10­24 were tested in vitro against NF-jB-luc 293 cell line induced by LPS. Compounds 12, 15, 16, 19, 21, and 23 exhibited moderate anti-inflammatory activities.

Three new olean-type triterpenoid saponins from aerial parts of Eclipta prostrata (L.).

Three new olean-type triterpenoid saponins, namely 3-O-(2-O-acetyl-ß-D-glucopyranosyl) oleanolic acid-28-O-(ß-D-glucopyranosyl) ester (1), 3-O-(6-O-acetyl-ß-D-glucopyranosyl) oleanolic acid-28-O-(ß-D-glucopyranosyl) ester (2) and 3-O-(ß-D-glucopyranosyl) oleanolic acid-28-O-(6-O-acetyl-ß-D-glucopyranosyl) ester (3), were isolated from the aerial parts of Eclipta prostrata (L.). Their structures were elucidated based on 1D and 2D NMR and MS spectroscopic data.

Two new triterpenoids from Ampelopsis japonica (Thunb.) Makino.

Two new triterpenoids were isolated from the ethanolic extract of the roots of Ampelopsis japonica (Thunb.) Makino. Their structures were defined as 3α-trans-feruloyloxy-2α-O-acetylurs-12-en-28-oic acid (1) and methyl 3α-trans-feruloyloxy-2α-hydroxyurs-12-en-28-oate (2) on the basis of spectral analysis.

Two New 3,4;9,10-seco-Cycloartane Type Triterpenoids from Illicium difengpi and Their Anti-Inflammatory Activities.

A pair of new 3,4;9,10-seco-cycloartane type triterpenoid stereoisomerides: 24R,25-dihydroxy-3,4;9,10-seco-4(28)-cycloarten-10,3-olide (1) named Illiciumolide A and 24S,25-dihydroxy-3,4;9,10-seco-4(28)-cycloarten-10,3-olide (2) named Illiciumolide B were isolated from the stem bark of Illicium difengpi, as well as five known biogenetically related triterpenoids, including sootepin E (3), betulinic acid (4), lupeol (5), (all-Z)-1,5,9,13,17,21-hexamethyl-1,5,9,13,17,21-cyclotertracosahexaene (6), and (all-E)-2,6,10,15,19,23-hexamethyl-2,6,10,14,18,22-tetracosahexaene (7). The structures of two new compounds were determined on the basis of spectroscopic analysis including 1D-, 2D-NMR, and MS techniques. Two assays were conducted: inhibition of tumor necrosis factor-alpha (TNF-α) and inhibition of nuclear factor kappa B (NF-κB) in RAW264. 7 cells induced by lipopolysaccharide (LPS). It was observed that compounds 1, 2 and 7 showed significant inhibition of TNF-α production and NF-κB release. The molecule docking results showed that compounds 1 and 2 got high fitness scores with dual specificity mitogen-activated protein kinase kinase 1 (MPKK1), whose activation plays a pivotal role between TNF-α and activation of NF-κB. The anti-HIV-1 potency of compounds 1-5 was also discussed, in addition to the results of computer-aided screening for targets.

Heracleifolinosides A-F, new triterpene glycosides from Cimicifuga heracleifolia, and their inhibitory activities against hypoxia and reoxygenation.

Six new 9,19-cycloartane triterpene glycosides, heracleifolinosides A-F (1-6), and one new chromone, norkhelloside (7), were isolated from the rhizome of Cimicifuga heracleifolia, together with 15 known compounds (8-22). The structures of the new compounds were elucidated by means of spectroscopic methods including 2D NMR and mass spectrometry. The extracts of C. heracleifolia and all the isolated compounds were tested for activities against hypoxia and reoxygenation injury in human umbilical vein endothelial cells. Heracleifolinoside B (2) is effectively resistant to hypoxia and reoxygenation-induced human umbilical vein endothelial cell injury, with cell viabilities of 61.95 ± 2.04 %, 77.04 ± 4.44 %, and 83.65 ± 3.29 % at concentrations of 1, 10, and 100 µM, respectively.